Memorable Letterman Moments

A Look Back At The Most Memorable Moments From 30 Years Of David Letterman

The Late Show with David Letterman has been an institution on television for 30 years and it’ll be hard to imagine television without him. Letterman, one of the greatest television stars of all time, will be hosting his last show tonight. We’re paying homage to his retirement by remembering some of the most memorable moments on his shows — both good and bad — so join us for a trip down memory lane.

Drew Barrymore on David Letterman

David Letterman is known for his stoic, unflappable demeanor but there were a few times when his emotions emerged. One of those moments was when a perky Drew Barrymore appeared on the show in 1995. After finding out that it was his birthday, Barrymore asked the band for some blues, got up on Dave’s desk and flashed her boobs. Well, they do say the best birthday gifts are experiences you’ll remember forever.

Lady Gaga Eats Dave Letterman’s Paper

Lady Gaga did her fair share of shocking antics early on in her career and one those memorable moments happened at the Ed Sullivan Theater. While asking Gaga about her alleged digestion of Barbie dolls at one of her shows, Gaga tore into and digested one of Dave’s papers.

Letterman Admits To Having Office Sex

That awkward moment when you admit to having office sex…on national television. In 2009, Dave was being threatened by an extortionist who seemed to know a lot of his dark secrets and was ready to go public with them. After spending about 10 minutes explaining the “bizarre experience” with this blackmailer, Letterman admitted to the purported dirty deeds, which included having sex with women who work on the show.

"How’d You Like Being In Jail, Paris Hilton?"

There are times when Letterman is soft, smooth and surreptitious with his line of questioning but when Paris Hilton came on in 2007, he was quite direct. 20 seconds in…fourth question…“How’d you like being in jail?”

And like a bulldog on a bone, Dave wouldn’t let up — even though Paris was “over it” — as he continued with the line of questioning for most of the interview.

David Letterman's 9/11 Monologues

Over his 30-year run, there were endless laughs on the Letterman show but his first show after the September 11th attacks in 2001 was a solemn one. Letterman opened the show with a sincere monologue, delivered with visible emotion. He told heartfelt stories about the impact of Mayor Rudy Giuliani’s courage and of a small town in Montana that donated money to New York City.

Letterman's Bizarre Interview With Joaquin Phoenix

Joaquin Phoenix threw everyone for a loop when he showed up to the Letterman Show completely unkempt, unshaved and wearing shades. As Phoenix gave curt answers and told everyone he’s retiring from acting, the general assumption was that he was high on some sort of drug. At any rate, Letterman and his dry humor still made this palatable. Phoenix would later return in 2010 and apologize for his previous behavior.

The Very First Letterman Episode: Comedy With Bill Murray

Talk about getting things off on the right foot. Bill Murray joins David Letterman for his first episode ever and the two made comedic magic. From absurdity, to sheer comedy, to endless sarcasm, this was a classic that still stands the test of time.

Letterman Interviews Madonna

Breaking news: Madonna has a rebellious side. In her 1994 interview with David Letterman, she refused to cooperate, swearing multiple times on live television and ripping into the host continuously. As per usual with Madonna’s stunts, they attracted attention. The interview turned out to be one of the show’s highest-rated ones of all-time.

Letterman Roasting John McCain

Senator John McCain was the GOP nominee for President in 2008 and was supposed to appear on the Late Show just months before the election. However, he canceled last-minute with a phony excuse, saying he had to rush to the airport on official business. Instead, Letterman caught him on CBS doing an interview with Katie Couric instead. Letterman comedically ripped him for 10 straight minutes on the show and the segment will go down among the best ever.

Cher Calls David Letterman An Asshole

Cher was a guest that the Late Show was trying to track down since the beginning but it took them four years to get her in the chair. And when she showed up, she caught everyone by surprise with her response. Start watching at the 3:50 mark to hear her thoughts.

Lindsay Lohan Cries On Letterman

Lindsay Lohan has been through her fair share of trials and tribulations, and she thought a good idea for a clean slate was an appearance on the Late Show. Although Dave is sometimes known as tossing softballs and pandering to guests, this was one interview where he put his guest on the grills. However, by the end of the interview, he made us feel sorry for Ms. Lohan as the tears started to roll.

Farah Fawcett's Drugged Up (?) Letterman Appearance

From the moment that she was barely able to walk out on the set, everyone could tell something was off with Farah Fawcett. And then the interview began. She was spacey, twitchy, and everything was just feel-good. Maybe ecstasy?

Michael Richards' Infamous Apology On Letterman

Michael Richards, famously known as Kramer on Seinfeld, joined the Late Show via satellite as Jerry Seinfeld was on-set in 2006 to apologize for his racist outburst at a comedy club. Well, an apology was given by Kramer — but it was a hard-to-watch, awkward segment.

Late Show Devoted To Warren Zevon

One of Dave’s more emotional interviews was when musician Warren Zevon came on the show. He was diagnosed with a terminal type of cancer and he was the only guest as the whole show was devoted to him. Zevon’s shared some inspirational advice, to “enjoy every sandwich, every moment and playing with the guys…” Later, he performed what would be his last public show. Unfortunately, he passed away within a year of that appearance.

Tina Fey Strips Down To Her Spandex

Although this memorable moment is more recent, who will ever forget Tina Fey stripping down to her spandex in front of David Letterman? Letterman helped unzip her out of her #LastDressEver and then appeared dumbfounded as she sat around in her special underwear.

Letterman's Tribute To Johnny Carson

The business of television can be quite competitive as everyone chases ratings, subscribers and online views. It was a refreshing break from that ego-driven mentality back in 2005 when Dave made his tribute to former great, Johnny Carson. He spoke of how he inspired him and gave him his first break in a touching segment of admiration.

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